9,10-dihydroxy-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide

• ChemBase ID: 167786
• Molecular Formular: C15H12N2O3
• Molecular Mass: 268.26738
• Monoisotopic Mass: 268.08479225
• SMILES: c12c(cccc1)N(c1c(cccc1)C(=C2O)O)C(=O)N
• Canonical SMILES: NC(=O)N1c2ccccc2C(=C(c2c1cccc2)O)O
• InChI: InChI=1S/C15H12N2O3/c16-15(20)17-11-7-3-1-5-9(11)13(18)14(19)10-6-2-4-8-12(10)17/h1-8,18-19H,(H2,16,20)
• InChIKey: ZDQLVKTWIHTZOE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9,10-dihydroxy-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide
• IUPAC Traditional name: 9,10-dihydroxy-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaene-2-carboxamide
• Synonyms: 10,11-Dihydroxy-5H-Dibenz[b,f]azepine-5-carboxamide; 10-Monohydroxy Oxcarbazepine; 10,11-Dihydroxy Carbamazepine DISCONTINUED

Database IDs

• CAS Number: 104839-39-6
• PubChem SID: 162261919
• PubChem CID: 10061548

CALCULATED PROPERTIES

• Acid pKa: 7.3095064
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 1.2522641
• LogD (pH = 7.4): 0.9110964
• Log P: 1.2589366
• Molar Refractivity: 75.6726 cm^3
• Polarizability: 28.15673 Å^3
• Polar Surface Area: 86.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452315

A metabolite of Carbamazepine (C175840) and Oxcarbazepine (O869250).

REFERENCES

• Madden, S., et al.: Drug Metab. Dispos., 24, 469, (1996)